Chicago Night Crimes Tour by Bus - The Biograph Theatre and the Chicago Skyline Highlights

Chicago Night Crimes Tour by Bus

Discover Chicago's dark side on a 2.5-hour bus tour featuring mobsters, crime scenes, historic landmarks, and exclusive crime museum visits for $55.

Discover Chicago’s Mobster Nightlife on a Two-and-Half-Hour Bus Tour

The Chicago Night Crimes Tour by Bus offers an engaging glimpse into the city’s notorious criminal past for just $55 per person. Spanning approximately 2 hours to 2.5 hours, this guided evening tour takes passengers through famous crime scenes, historic landmarks, and hidden tunnels associated with Chicago’s most infamous gangsters like Al Capone, Frank Nitti, and Bugs Moran. It departs from the southeast corner of N. Michigan Avenue and E. Pearson Street at 7:30 pm, making it ideal for those seeking a captivating night activity.

This tour stands out for its live narration by experienced guides, stopping at key crime locations with opportunities to get off the bus and explore. While it offers rich stories and interesting sights, note that the bus is not wheelchair accessible, and there are no restroom breaks. With an average booking window of two weeks, this experience appeals to those who want a deep dive into Chicago’s criminal history combined with some city sightseeing.

Key Points

Chicago Night Crimes Tour by Bus - Key Points

  • Price is $55 per person for a 2 to 2.5-hour guided tour.
  • Departs at 7:30 pm from N. Michigan Avenue and Pearson Street.
  • The tour includes stops at crime scenes, landmarks, and a crime museum.
  • Guides are informative, personable, and knowledgeable.
  • Tour features live narration, photo opportunities, and historic video footage.
  • Not suitable for those needing wheelchair access or restroom breaks.

Starting Point and Tour Schedule in Downtown Chicago

The tour begins outside 163 E. Pearson Street, right across from the Museum of Contemporary Art, which makes it easy to find and accessible via public transportation. The meet-up at 7:30 pm is punctual, and arriving 15 minutes early is recommended to find your seat comfortably. The tour concludes back at the starting point, offering a convenient and central finish.

The bus is temperature-controlled and designed for comfort, with the guides providing a lively, engaging commentary throughout. The small maximum group size of 39 travelers ensures an intimate experience, although the first-come, first-served seating means early arrival is best.

Exploring Chicago’s Infamous Crime Scenes and Landmarks

Chicago Night Crimes Tour by Bus - Exploring Chicagos Infamous Crime Scenes and Landmarks

During the 2.5-hour tour, travelers visit famous crime sites such as the scene of the St. Valentine’s Day Massacre, the handshake murder location, and The Enforcers’ Safe and tunnels. Guests are encouraged to get off the bus at each stop to observe and photograph these historic locations, which makes the experience more tangible.

The tour also passes by notable buildings including Jewelers Building, Thirty Five E Wacker, and Harry Caray’s Italian Steakhouse. The latter features Nitti’s Vault, a crime museum, and a bootlegging tunnel, providing an intriguing look into Chicago’s Prohibition-era crimes.

The Biograph Theatre and the Chicago Skyline Highlights

Chicago Night Crimes Tour by Bus - The Biograph Theatre and the Chicago Skyline Highlights

A key attraction is the visit to the Biograph Theatre, famous for its association with John Dillinger. Passengers get a chance to see the historic landmark and learn about Dillinger’s last moments. The drive across Lakeshore Drive offers beautiful views of the lake and city skyline, with sights like Oz Park and the Water Tower, which survived the Great Chicago Fire of 1871.

The State Street Bridge provides spectacular vantage points of the Chicago River, enhancing the sightseeing component of this crime-themed tour.

Inside Nitti’s Vault and the Prohibition Tunnels

Chicago Night Crimes Tour by Bus - Inside Nitti’s Vault and the Prohibition Tunnels

Part of the tour includes visiting Harry Caray’s Italian Steakhouse, where Nitti’s Vault functions as a crime museum. Here, guests see historical artifacts and learn about Chicago’s bootlegging tunnels used during Prohibition. The stories behind these tunnels and the city’s underground crime network add a layer of mystery and authenticity to the experience.

The Final Stops: Holy Name Cathedral and the Water Tower

The tour concludes with a walk past Holy Name Cathedral, where gangster Hymie Weiss‘s last steps are vividly recounted. Just across from the Historic Water Tower, the tour wraps up, giving visitors a chance to view one of the few surviving structures from the Chicago Fire, enriching the historical context.

The Guide’s Role in Making the Tour Memorable

Chicago Night Crimes Tour by Bus - The Guide’s Role in Making the Tour Memorable

Reviews consistently praise the guides for their expertise and engaging storytelling. Guides like Kathryn and John receive high marks for their personable, enthusiastic, and well-prepared narration. They share interesting facts, stories about gangsters, and details about crime scenes, making the tour both entertaining and educational.

Many guides also recommend books or shows related to Chicago crime, encouraging further exploration. Their ability to keep the group moving and handle unexpected issues, like weather challenges, adds to the overall positive experience.

Practical Tips and Considerations

Since the bus is not wheelchair accessible and lacks restroom facilities, travelers should arrive early and go to the bathroom beforehand. The tour is conducted in the evening, so visibility of buildings is limited, which some reviews note as a drawback. No food or drinks are permitted on the bus, but a pizza treat at the end offers a small bonus, though the main focus remains on crime history.

Guests are advised to dress comfortably for the evening, especially if the weather turns foggy or chilly. Given that the tour is most popular for those interested in history, crime, and Chicago’s architectural landmarks, it’s ideal for history buffs and crime enthusiasts.

Comparing Value and Overall Experience

At $55, this tour offers excellent value given the length, stops, and guided narration. The inclusion of photo opportunities, historic videos, and access to Nitti’s Vault enhances the experience. The small group size and live guide commentary make it more immersive than a simple bus ride.

While some reviews mention the tour ending early or not being ideal for daytime sightseeing, the nighttime ambiance adds a mysterious, atmospheric element to the experience. If you’re interested in Chicago’s criminal past and enjoy guided city tours, this activity provides a great mix of storytelling and sightseeing.

Chicago Night Crimes Tour: Who Will Enjoy It Most?

This tour is perfect for history enthusiasts, true crime fans, and urban explorers eager to see Chicago through a different lens. It appeals to those who enjoy guided storytelling, historic landmarks, and city views at night. However, travelers requiring disability access or rest breaks may find this tour less suitable.

The cost-effectiveness, informative guides, and fascinating crime stories make it a worthwhile experience for anyone looking for an entertaining evening activity in downtown Chicago.

✨ Book This Experience

Chicago Night Crimes Tour by Bus



5.0

(432 reviews)

88% 5-star

“The tour guide was very good & told us a lot of interesting information. The pizza was a nice surprise at the end of the tour.”

— Lorene H, Apr 2025

Frequently Asked Questions

Is this tour suitable for children?
While not specifically designed for children, the content is generally appropriate for older kids interested in crime stories and Chicago history.

Do I need to book in advance?
Yes, the tour is usually booked about 14 days ahead, and early booking is recommended to secure a spot due to limited seating.

Are there any discounts or special offers?
The standard ticket price is $55, and no mention of discounts is provided. The tour offers a full refund if canceled at least 24 hours in advance.

Can I join the tour late or leave early?
Guests cannot join after the bus departs, and early departure is not permitted, so arriving on time is essential.

What should I bring or wear?
Dress comfortably for an evening outdoor experience; be prepared for weather conditions and avoid eating or drinking on the bus.

This Chicago Night Crimes Tour offers a lively, well-guided exploration of the city’s criminal past, blending history, architecture, and true crime stories into a memorable night adventure.